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Discovery of New Catalytic System for Efficient Transformation of C–H Bonds

Research Project

Project/Area Number 26620083
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionNational Institute of Advanced Industrial Science and Technology (2016)
Kyoto University (2014-2015)

Principal Investigator

Yada Akira  国立研究開発法人産業技術総合研究所, 触媒化学融合研究センター, 研究員 (70619965)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords炭素-水素結合 / 不活性結合活性化 / パラジウム / 有機金属化学 / 炭素ー水素結合 / 炭素―水素結合 / 炭素-水素結合 / 脱水素型カップリング
Outline of Final Research Achievements

In order to improve the practicality and efficiency of the transition-metal catalyzed C-H bond functionalization reaction, new catalytic reactions that consist of the introduction of an activating group into an organic molecule, the bond formation reaction, and recycle of the activating group, were investigated. As the result, unexpected effect of salicylaldehyde which act as the multipurpose directing group that is easily available, installable, removable, and recoverable, for palladium-catalyzed arylation reaction of primary amines was developed. In addition, a palladium-catalyzed intramolecular insertion of alkenes into carbonyl C-N bonds of β-lactams affording nitrogen-containing fused bicyclic compounds was discovered.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (8 results)

All 2017 2016 2015 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 2 results) Presentation (5 results) Remarks (1 results)

  • [Journal Article] Buttressing Salicylaldehydes: Multipurpose Directing Group for C(sp3)-H Bond Activation2017

    • Author(s)
      Akira Yada, Wenqing Liao, Yuta Sato, Masahiro Murakami
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 4 Pages: 1073-1076

    • DOI

      10.1002/anie.201610666

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Intramolecular Insertion of Alkenes into the Carbon-Nitrogen Bond of β-Lactams2015

    • Author(s)
      Akira Yada, Satoshi Okajima, Masahiro Murakami
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 27 Pages: 8708-8711

    • DOI

      10.1021/jacs.5b05308

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] サリチルイミンを配向基として用いる第一級アミン化合物の炭素―水 素結合のワンポットアリール化およびアルキル化反応2016

    • Author(s)
      矢田陽、寥文卿 、石原優実、佐藤裕太、村上正浩
    • Organizer
      日本プロセス化学会 2016 サマーシンポジウム
    • Place of Presentation
      愛知県名古屋市
    • Year and Date
      2016-07-28
    • Related Report
      2016 Annual Research Report
  • [Presentation] Salicylimine as a Directing Group for γ-C(sp3)-H Arylation of Amino Groups2016

    • Author(s)
      Wenqing Liao, Yumi Ishihara, Yuta Sato, Akira Yada, Masahiro Murakami
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] サリチルイミンを配向基として用いるC(sp2)-H結合のアリール化およびアルキル化反応2016

    • Author(s)
      石原優実、廖文卿、佐藤裕太、矢田陽、村上正浩
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] サリチルイミンを配向基として用いるアミノ基のγ位炭素-水素結合のアリール化およびアルキル化反応2015

    • Author(s)
      矢田陽、佐藤裕太、廖文卿、石原優実、村上正浩
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス(大阪府吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] Palladium-catalyzed Intramolecular Alkene Insertion into Carbon-Nitrogen Bonds of β-Lactams2015

    • Author(s)
      OKAJIMA, Satoshi; Yada, Akira; Murakami, Masahiro
    • Organizer
      日本化学会第95春季年会(2015)
    • Place of Presentation
      船橋市 日本大学
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Remarks] 京都大学 工学研究科 合成・生物化学専攻 村上研究室のホームページ

    • URL

      http://www.sbchem.kyoto-u.ac.jp/murakami-lab/index.html

    • Related Report
      2015 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

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